1,4,7,10,13-pentaoxacyclopentadecane-2,6-dione
15-crown-5
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 79% |
Pentaethylene glycol
15-crown-5
Conditions | Yield |
---|---|
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 80℃; | 75% |
With sodium hydroxide; p-toluenesulfonyl chloride In 1,2-dimethoxyethane at 0℃; Product distribution; var. solvents, reagents, and temp.; other oligoethylene glycols; | 36 % Chromat. |
Conditions | Yield |
---|---|
With sodium carbonate; dicyclohexyl-carbodiimide In 1,4-dioxane at 70 - 75℃; for 6h; Concentration; Reagent/catalyst; Temperature; Solvent; | 70.2% |
3-oxa-1,5-dichloropentane
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
15-crown-5
Conditions | Yield |
---|---|
With sodium methylate In 1,4-dioxane for 24h; Heating; metal hydroxides, different bases as 'template' agents; | 66% |
With sodium methylate In 1,4-dioxane for 24h; Heating; | 66% |
1,4,7,10,13-Pentaoxacyclopentadecane-2,3-dithione
15-crown-5
Conditions | Yield |
---|---|
With nickel In diethyl ether; dichloromethane at 0℃; for 1h; | 52% |
Pentaethylene glycol
A
15-crown-5
B
<60>crown-20
C
<30>crown-10
D
45-Crown-15
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; | A 46% B 0.7% C 12% D 3.4% |
Pentaethylene glycol
A
15-crown-5
B
<30>crown-10
C
45-Crown-15
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; | A 46% B 12% C 3.4% |
Conditions | Yield |
---|---|
With potassium hydroxide for 0.133333h; microwave irradiation; | 40% |
diethylene glycol ditosylate
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
15-crown-5
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature; | 25% |
Conditions | Yield |
---|---|
In benzene at 25℃; Equilibrium constant; |
complex of 15-crown-5 with K+
15-crown-5
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; | |
In acetone at 25℃; Equilibrium constant; complexation of alkali metal cations (Li+, Na+, K+, Rb+, Cs+) with crown ethers, diaza crown ethers and cryptands in acetone, stability constants of complexes formed; influence of ion-pair formation on stability constants; |
complex of 15-crown-5 with Na+
15-crown-5
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In methanol; water at 25℃; Equilibrium constant; var. MeOH/H2O ratio; |
Conditions | Yield |
---|---|
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane; water at 25℃; for 0.666667h; Equilibrium constant; |
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.); |
A
15-crown-5
B
1-(2-chlorophenyl)ethanone
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 20℃; Rate constant; Kinetics; Thermodynamic data; var. crown ethers, ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
triethylene glycol di-(p-toluenesulfonate)
diethylene glycol
15-crown-5
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature; | 33 % Chromat. |
15-crown-5
Conditions | Yield |
---|---|
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, propylene carbonate, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, 7Li NMR study; | |
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, MeOh H2O etc.), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes; |
15-crown-5
Conditions | Yield |
---|---|
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0; |
Conditions | Yield |
---|---|
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0; |
Conditions | Yield |
---|---|
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG0; |
15-crown-5
[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
sodium hexamethyldisilazane
[(OC)5WP(CH(SiMe3)2)CNNa(15-crown-5)]
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; cooled (-80°C) soln. of NaN(SiMe3)2 in THF added dropwise to stirred soln. of W complex in THF and 15-crown-5; warmed slowly toroom temp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.; | 100% |
15-crown-5
Conditions | Yield |
---|---|
With sodium bromide In water at 20℃; for 12h; | 100% |
15-crown-5
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 12h; | 100% |
15-crown-5
Conditions | Yield |
---|---|
With sodium iodate In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 15-crown-5; sodium chloride In water at 20℃; for 12h; Stage #2: zinc(II) chloride In ethanol for 12h; Reflux; | 100% |
15-crown-5
sodium chloride
Conditions | Yield |
---|---|
Stage #1: 15-crown-5; sodium chloride In water at 20℃; for 12h; Stage #2: iron(III) chloride hexahydrate In ethanol for 12h; Reflux; | 100% |
Conditions | Yield |
---|---|
In water UO2OAc2*2H2O, NaCH3COO, ligand and HCl were combined in water with stirring, evapd. slowly at room temp. for 1 wks; isolated; elem. anal.; | 99.9% |
15-crown-5
[NaU(bis(trimethylsilyl)amide)(CH2SiMe2N(SiMe3))2]
Conditions | Yield |
---|---|
In pentane under Ar; a NMR tube was charged with U-contg. compd. (0.027 mmol) in pentane, and 15-crown-5 (0.032 mmol) was added; the suspn. was heated for 3 d at 60°C; elem. anal.; | 99% |
15-crown-5
1,1,1-trimethyl-2,2,2-triphenyldisilane
Conditions | Yield |
---|---|
With sodium t-butanolate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane | 99% |
15-crown-5
zirconium(IV) chloride
Conditions | Yield |
---|---|
In acetonitrile soln. of ZrCl4 and 15-crown-5 prepared under cooling; addn. of NaF; stirred for 12 h at 25°C; filtration; solvent removed until beginning of crystn.; cooled down to 5°C; crystn.; filtration; washed (cold acetonitrile); dried under vac.; elem. anal.; IR; | 98.3% |
Conditions | Yield |
---|---|
In tetrachloromethane Ar-atmosphere; room temp.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
In pentane Ar; U compd. and ligand (1:1 molar ratio), stirred for 12 at 20°C; filtered, evapd., elem. anal.; | 98% |
iron(II) bis(trimethylsilyl)amide
15-crown-5
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
Stage #1: iron(II) bis(trimethylsilyl)amide; sodium hexamethyldisilazane In toluene for 1h; Reflux; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: 15-crown-5 In toluene for 1h; Reflux; Inert atmosphere; Glovebox; Schlenk technique; | 97.74% |
Conditions | Yield |
---|---|
With sodium t-butanolate In tetrahydrofuran; toluene Ambient temperature; | 97% |
Conditions | Yield |
---|---|
With hydrogenchloride In water addn. of org. ligand to soln. of ammonium dichromate and concd. hydrochloric acid (stirring, 20°C); ppt. filtered off, washed (water) and dried at 40-50°C; elem. anal.; | 97% |
15-crown-5
sodium thiophenolate
Conditions | Yield |
---|---|
In tetrahydrofuran N2-atmosphere; mixing Ni-complex with excess NaSPh, addn. of MeOH, stirring for 1 d, filtration, addn. of excess of crown; crystn. (-30°C, 3 d), collection (filtration), washing (THF, hexane), drying (vac., 2 h); elem. anal.; | 97% |
15-crown-5
C10H20O5*C24H25F4Si(1-)*Na(1+)
Conditions | Yield |
---|---|
With sodium fluoride In toluene for 648h; Inert atmosphere; | 97% |
15-crown-5
Conditions | Yield |
---|---|
In tetrahydrofuran standard inert-atmosphere techniques; soln. of (15)crown-5 (0.972 mmol) added to soln. of Sn(OTf)2 (0.480 mmol), stiired for 2 h; solvent removed (in vac.), washed with pentane; elem. anal.; | 97% |
15-crown-5
Conditions | Yield |
---|---|
In tetrahydrofuran | 96.1% |
In tetrahydrofuran byproducts: THF; under N2 15-crown-5 was added dropwise to THF soln. of Mg-compd.; ppt. was centrifuged off, dried in vac., elem. anal.; | 96.1% |
15-crown-5
MoF4(NCl)
Conditions | Yield |
---|---|
In acetonitrile stirring (room temp., 2 h); crystn. on cooling (-18°C), sepn. (filtration off), washing (acetonitrile), drying (vac.); elem. anal.; | 96% |
Conditions | Yield |
---|---|
In tetrachloromethane Ar-atmosphere; molar ratio Nb2Cl10:crown=1:2, room temp.; elem. anal.; | 96% |
2-(3-methoxymethoxyphenyl)butane-1,2-diol
15-crown-5
methyl iodide
2-methoxy-2-(3-methoxymethoxyphenyl)but-1-yl methyl ether
Conditions | Yield |
---|---|
In N-methyl-acetamide; mineral oil | 95% |
15-crown-5
Conditions | Yield |
---|---|
In acetonitrile byproducts: NaCl; addn. of NaF to suspn. of Mo-complex, addn. of 15-crown-5 (dropwise), stirring (12 h), sepn. of ppt. (filtration); crystn. on cooling (-20°C), sepn. (filtration off), washing (acetonitrile), drying (vac.); elem. anal.; | 95% |
15-crown-5
acetonitrile
Conditions | Yield |
---|---|
In acetonitrile heating of 1.8mmol (ReCl3(NO)2)2 in 30ml acetonitrile (formation of sol. (ReCl3(NO)2(CH3CN)), addn. of 3.6mmol NaF amd 0.715ml 15 crown-5; 2h refluxing;; cooling down and concg. of soln.; single crystal;filtn., concgn. of filtrate (20ml); elem. anal.;; | 95% |
aluminium trichloride
15-crown-5
{AlCl2((CH2CH2O)5)}(1+)*AlCl4(1-)={AlCl2((CH2CH2O)5)}{AlCl4}
Conditions | Yield |
---|---|
In tetrahydrofuran all manipulations under dry N2; slowly dissolving AlCl3 in THF, adding 15-crown-5 with stirring, color change from light green to dark green, crystn. (after 30 min); sepg. crystals from the mother soln., drying (vac., 25°C); elem. anal.; | 95% |
15-crown-5
(ScCl2(C10H20O5))(1+)*Cl(1-)=(ScCl2(C10H20O5))Cl
Conditions | Yield |
---|---|
In acetonitrile Sc-compd. was dissolved in MeCN (under dry inert gas), addn. of crown ether; sepn. of precipitate, washing with MeCN, vac. drying at 30°C, elem. anal.; | 95% |
IUPAC Name: 3,6,9,12,15-Pentaoxacyclopentadecane
Molecular Formula: C10H20O5
Molecular Weight: 220.26 g/mol
Canonical SMILES: C1COCCOCCOCCOCCO1
InChI: InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
EINECS: 251-379-6
Classification Code: Drug / Therapeutic Agent; Skin / Eye Irritant
Product Categories: Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry
Stability: Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.
Water Solubility: Miscible
Sensitive: Hygroscopic
XLogP3: -0.5
H-Bond Acceptor: 5
Index of Refraction: 1.404
Molar Refractivity: 54.14 cm3
Molar Volume: 221.3 cm3
Polarizability: 21.46×10-24 cm3
Surface Tension: 31.2 dyne/cm
Density: 0.995 g/cm3
Flash Point: 139.1 °C
Enthalpy of Vaporization: 57.2 kJ/mol
Boiling Point: 350.9 °C at 760 mmHg
Water Solubility: 8.82E+04 mg/L at 25 °C
Henry's Law Constant: 2.22E-11 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 7.01E-11 cm3/molecule-sec at 25 °C
Vapour Pressure of 15-Crown-5 (CAS NO.33100-27-5): 1.44E-03 mm Hg at 25 °C
15-Crown-5 (CAS NO.33100-27-5) is used as phase transfer catalyst, metal complexing agent, selective removal and separation of cation.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 514mg/kg (514mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
mouse | LD50 | oral | 1020mg/kg (1020mg/kg) | BEHAVIORAL: TREMOR | Toxicology and Applied Pharmacology. Vol. 44, Pg. 263, 1978. |
rabbit | LD50 | intraperitoneal | 560mg/kg (560mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987. | |
rabbit | LD50 | skin | 2520mg/kg (2520mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
rat | LD50 | intraperitoneal | 530mg/kg (530mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
rat | LD50 | oral | 1410mg/kg (1410mg/kg) | BEHAVIORAL: TREMOR | Drug and Chemical Toxicology. Vol. 1, Pg. 339, 1978. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:Xn, Xi
Risk Statements: 22-36/38-36-20/22-36/37/38-20/21/22
R22: Harmful if swallowed.
R36/38: Irritating to eyes and skin.
R36: Irritating to eyes.
R20/22: Harmful by inhalation and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39: Wear eye / face protection.
S36: Wear suitable protective clothing.
RIDADR: 2810
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup of 15-Crown-5 (CAS NO.33100-27-5): III
15-Crown-5 (CAS NO.33100-27-5), its Synonyms are 1,4,7,10,13-Pentaoxacyclopentadecane ; 15-Crown-5,1,4,7,10,13-Pentaoxa-cyclo-pentadecane ; Crownethers ; Ethyleneoxidecyclicpentamer ; Lead ionophore V . It is colourless liquid. It is a cyclic pentamer of ethylene oxide that has been shown to complex with various cations, including sodium (Na+) and potassium (K+), but selective binding to lead (Pb2+).
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